Novel deordorising compositions and deodorising products containing same

ABSTRACT

The invention relates to novel deodorant compositions containing at least one compound of the family of acetylenic ketones and the deodorant products containing them. A particularly preferred composition according to the invention comprises at least one compound of the family of the α-acetylenic ketones and a mixture of aldehydes chosen from two different families.

The present Application relates to novel deodorant compositionscontaining at least one compound of the family of acetylenic ketones andthe deodorant products containing them.

Combating unpleasant odours has led to the use of numerous widelyvarying substances, for example phenolic substances, essential oils,resins, aldehydes or ketones, alcohol derivatives, esters or others.

Various aldehydes have in particular been used, alone or mixed withnumerous other products. Although satisfactory, these products do notalways have the desired effectiveness.

A need therefore still exists for more effective deodorant compositions,optionally with a pleasant smell.

After lengthy work, the Applicant has discovered that molecules of thefamily of acetylenic ketones can be used in deodorant compositions,particularly due to their property of destroying malodorous molecules.It is therefore understood that in the present text the use of theexpression “deodorant composition” refers to a composition the deodoranteffect of which is linked to the properties of physical destruction ofthe malodorous molecules by the acetylenic ketones and not to anymasking of the unpleasant odour.

In the remainder of the present text, the expression “acetylenic ketone” is used to denote chemical molecules comprising at least oneketo-α-acetylenic chain formation (—CO—C≡C— or —C≡C—CO—).

Thus the first subject of the invention is a deodorant compositioncharacterized in that it comprises at least one compound of the familyof the α-acetylenic ketones corresponding to general formula 1

R—(CO)_(k)—C≡C-(A)-(C≡C)_(m)—(CO)_(n)—R₁   (1)

in which

-   -   R and R₁ can represent, independently or simultaneously, a        radical chosen from        -   an alkyl chain comprising from 1 to 9, preferentially from 3            to 7 carbon atoms, linear or branched, substituted or            unsubstituted, or        -   a cycloalkane comprising from 3 to 8, preferentially 5 or 6            carbon atoms, substituted or unsubstituted; or        -   a furan ring, saturated or unsaturated, substituted or            unsubstituted; or        -   a pyran ring, saturated or unsaturated, substituted or            unsubstituted; or        -   an aromatic ring comprising from 6 to 8 carbon atoms,            substituted or unsubstituted; or also        -   a hydrogen atom.    -   A represents a group chosen from —(CH₂)_(x) with x representing        an integer with a value from 0 to 6, preferentially from 0 to 4,        (—CO)_(I) with I representing an integer with a value of 0 or 1,        or also a —(CH₂)_(y)—O—(CH₂)_(z)— chain formation with y and z        representing, simultaneously or independently, an integer with a        value from 0 to 6, preferentially from 0 to 4, it being        understood that x+y does not exceed the value of 6;    -   k, m and n are, simultaneously or independently, an integer with        a value of 0 or 1, it being understood that k and n cannot        simultaneously have a value of 0 if I is equal to 0.

with the exception of 2-methyl-4-nonyn-3-one of formulaC₄H₉—C≡C—CO—CH(CH₃)₂.

According to the invention, by alkyl chain comprising from 1 to 9 carbonatoms is meant a methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl,octyl, nonyl radical, linear or branched, substituted or unsubstituted,in particular by one or more oxo group(s), however without the totalcarbon atoms in the molecule exceeding 18, preferentially 16.

Also according to the invention, by a cycloalkane comprising from 3 to 8carbon atoms is meant a cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, cyclopropylcarbonyl,cyclobutylcarbonyl, cyclopropylmethyl or also cyclobutylmethyl radical.

Also according to the invention, by an aromatic ring comprising from 6to 8 carbon atoms is meant a radical chosen from phenyl, benzyl orphenethyl, optionally substituted by one or two substituents, identicalor different, chosen from the methyl, dimethyl, methoxy, dimethoxy,hydroxy, acetyl, cyano substituents.

According to the invention, the R and R₁ radicals can be simultaneouslyor independently substituted by one or more radicals chosen from themethyl, ethyl, propyl, butyl radicals or also a 2-oxopropyl radical.

Advantageously according to the invention, R and R1 can bepreferentially an acetonyl, pentyl, hexyl, heptyl, cyclopropyl,cyclopentyl, cyclohexyl, furyl or phenyl, anisyl, dimethoxyphenyl, tolylradical and R₁ can be a hydrogen atom.

According to the invention, the compound of formula 1 can be present inthe composition in a quantity comprised between 0.01% and 40%,preferentially between 0.1% and 15%, even more preferentially from 1% to10% of the total weight of the composition.

According to the invention, the composition can comprise one or morecompounds corresponding to formula 1.

According to the invention, it is possible to use preferentially in thecompositions at least one of the compounds chosen from:

-   -   1-octyn-3-one of formula C₅H₁₁—CO—C≡CH;    -   3-octyn-2-one of formula C₄H₉—C≡C—CO—CH_(3;)    -   4-octyn 3-one of formula C₃H₇—C≡C—CO—C₂H₅;    -   4-nonyn-3-one of formula C₃H₇—CH₂—C≡C—CO—C₂H₅;    -   2-nonyn-4-one of formula CH₃—C≡C—CO—C₅H₁₁;    -   5-nonyn-4-one of formula C₃H₇—CO—C≡C—CH₂—C₂H₅;    -   1-decyn-3-one of formula C₇H₁₅—CO—C≡CH;    -   4-decyn-3-one of formula C₅H₁₁—C≡C—CO—C₂H_(5;)    -   6-decyn-5-one of formula C₃H₇—C≡C—CO—C₄H₉;    -   5-decyn-4-one of formula C₄H₉—C≡C—CO—C₃H₇;    -   2-decen-5-yn-4-one of formula C₄H₉—C≡C—CO—CH═CH—CH₃;    -   1-(p-methoxyphenyl)-2-propyn-1-one of formula        H₃C—O—C₆H₄—CO—C≡CH;    -   1-cyclopropyl-2-heptyn-1-one of formula C₄H₉—C≡C—CO—C₃H₅        cyclopropyl);    -   2-methyl-5-decyn-4-one of formula C₄H₉—C≡C—CO—CH₂—CH(CH₃)₂;    -   9-methyl-5-decyn-4-one of formula        C₃H₇—CO—C≡C—CH₂—CH₂—CH(CH₃)_(2;)    -   2-methyl-4-octyn-3-one of formula C₃H₇—C≡C—CO—CH(CH₃)₂;    -   1-phenyl-2-propyn-1-one of formula C₆H₅—CO—C≡CH;    -   4-phenyl-3-butyn-2-one of formula C₆H₅—C≡C—CO—CH_(3;)    -   5-phenyl-4-pentyn-3-one of formula C₆H₅—C≡C—CO—C₂H₅;    -   6-phenyl-5-hexyn-2,4-dione of formula C₆H₅—C≡C—CO—CH₂—CO—CH₃;    -   1-phenyl-1-heptyn-3-one of formula C₆H₅—C≡C—CO—C₄H_(9;)    -   1-(2-furyl)-3-phenyl-2-propyn-1-one of formula C₆H₅—C≡C—CO—C₄H₃O        furyl);    -   1-(2-furyl)-2-octyn-1-one of formula C₅H₁₁—C≡C—CO—C₄H₃O (furyl);    -   C₆H₅—C≡C—CO—C₄H₃O (furyl);    -   3-cyclopropyl-1-(p-tolyl)-2-propyn-1-one of formula        C₃H₂—C≡C—CO—C₆H₄—CH₃;    -   1-cyclopropyl-4-methyl-1-hexyn-3-one of formula        C₃H₅—C≡C—CO—CH(C₂H₅)—CH₃(cyclopropyl);    -   9-hexadecyn-8-one of formula C₆H₁₃—C≡C—CO—C₇H₁₅;    -   5-ethyl-11-methyl-7-dodecyn-6-one of formula        (CH₃)₂CH—C₂H₄—C≡C—CO—CH(C₂H₅)—C₄H_(9;)    -   7-tetradecyn-6-one of formula C₆H₁₃—C≡C—CO—C₅H_(11;)    -   1-cyclohexyl-4-ethyl-1-hexyn-3-one of formula        C₆H₁₁—C≡C—CO—CH(C₂H₅)₂(cyclohexyl);    -   1-cyclopentyl-4-nonyn-3-one of formula        C₄H₉—C≡C—CO—C₂H₄—C₅H₉(cyclopentyl);    -   1-cyclohexyl-2-heptyn-1-one of formula        C₄H₉—C≡C—CO—C₆H₁₁(cyclohexyl);    -   1-(p-tolyl)-2-butyn-1-one of formula CH₃—C≡C—CO—C₆H₄-(p-CH₃)_(;)    -   2,2,8-trimethyl-4-nonyn-3-one of formula        (CH₃)₂CH—C₂H₄—C≡C—CO—C(CH₃)₃;    -   2,2-dimethyl-4-hexyn-3-one of formula CH₃—C≡C—CO—C(CH₃)_(3;)    -   1,4-diphenyl-2-butyn-1,4-dione of formula C₆H₅—CO—C≡C—CO—C₆H₅;    -   5-decyn-2,4-dione of formula C₄H₉—C≡C—CO—CH₂—CO—CH₃;    -   1-(3,4-dimethoxyphenyl)-2-butyn-1-one of formula        CH₃—C≡C—CO—C₆H₃—(OCH₃)₂;    -   2,5-heptadiyn-4-one of formula H₃C—C≡C—CO—C≡C—CH_(3;)    -   3-hexyn-2,5-dione of formula CH₃—CO—C≡C—CO—CH₃;    -   4-octyn-3,6-dione of formula C₂H₅—CO—C≡C—CO—C₂H₅;    -   2,7-dimethyl-4-octyn-3,6-dione of formula        (CH₃)₂CH—CO—C≡C—CO—CH(CH₃)₂;    -   2,7-dimethyl-4-octyn-3-one of formula        (CH₃)₂CH—CH₂—C≡C—CO—CH(CH₃)₂;    -   4,7-undecadiyn-6-one of formula C₃H₇—C≡C—CO—C≡C—C₃H₇;    -   5-decyn-4,7-dione of formula C₃H₇—CO—C≡C—CO—C₃H₇;    -   2,9-dimethyl-5-decyn-4,7-dione of formula        (CH₃)₂CH—CH₂—CO—C≡C—CO—CH₂—CH(CH₃)₂;    -   6-dodecyn-5,8-dione of formula C₄H₉—CO—C≡C—CO—C₄H_(9;)    -   2,11-dimethyl-6-dodecyn-5,8-dione of formula        (CH₃)₂CH—C₂H₄—CO—C≡C—CO—(CH₂)₂—CH(CH₃);    -   2,9-dimethyl-5-decyn-4-one of formula        (CH₃)₂CH—C₂H₄—C≡C—CO—CH₂—CH(CH₃)₂;    -   7-tetradecyn-6,9-dione of formula C₅H₁₁—CO—C≡C—CO—C₅H_(11;)    -   4,10-undecadiyn-3-one of formula HC≡C—C₄H₈—C≡C—CO—C₂H₅;    -   2,12-dimethyl-7-oxa-4,9-tridecadiyn-3,11-dione of formula        (CH₃)₂—CO—C≡C—CH₂—O—CH₂—C≡C—CO—CH(CH₃)₂, or also    -   4,10-tetradecadiyn-3,12-dione of formula        C₂H₅—CO—C≡C—C₄H₈—C≡C—CO—C₂H₅.

Very preferentially it is possible to use at least one compound chosenfrom

-   -   1-phenyl-2-propyn-1-one of formula C₆H₅—CO—C≡CH;    -   1-decyn-3-one of formula C₇H₁₅—CO—C≡CH;    -   1-(2-furyl)-2-octyn-1-one of formula C₅H₁₁—C≡C—CO—C₄H₃O (furyl);    -   1-(2-furyl)-3-phenyl-2-propyn-1-one of formula C₆H₅—C≡C—CO—C₄H₃O        (furyl);    -   1-octyn-3-one of formula C₅H₁₁—CO—C≡CH;    -   1-(p-tolyl)-2-butyn-1-one of formula CH₃—C≡C—CO—C₆H₄-(p-CH₃)_(;)    -   2,5-heptadiyn-4-one of formula CH₃—C≡C—CO—C≡C—CH_(3;)    -   1-(p-methoxyphenyl)-2-propyn-1-one of formula CH₃O—C₆H₄—CO—C≡CH;    -   1,4-diphenyl-2-butyn-1,4-dione of formula C₆H₅—CO—C≡C—CO—C₆H₅;        or also    -   4,7-undecadiyn-6-one of formula C₃H₇—C≡C—CO—C≡C—C₃H₇.

According to a variant of the invention, it is possible to use in thecompositions any combination of at least 2 of the compoundscorresponding to formula 1, preferentially those previously listed andeven more preferentially the pairs formed by 2 compounds chosen from thepairs:

-   -   1-phenyl-2-propyn-1-one/1-decyn-3-one;    -   1-(2-furyl)-2-octyn-1-one/1-decyn-3-one;    -   1-(2-furyl)-3-phenyl-2-propyn-1-one/1-decyn-3-one;    -   1-octyn-3-one/1-decyn-3-one;    -   1-(p-tolyl)-2-butyn-1-one/1-decyn-3-one;    -   2,5-heptadiyn-4-one/1-decyn-3-one;    -   1-(p-methoxyphenyl)-2-propyn-1-one/1-decyn-3-one;    -   1,4-diphenyl-2-butyn-1,4-dione/1-decyn-3-one;    -   4,7-undecadiyn-6-one/1-decyn-3-one;    -   1-(2-furyl)-2-octyn-1-one/1-phenyl-2-propyn-1-one;    -   1-(2-furyl)-3-phenyl-2-propyn-1-one/1-phenyl-2-propyn-1-one;    -   1-octyn-3-one/1-phenyl-2-propyn-1-one;    -   1-(p-tolyl)-2-butyn-1-one/1-phenyl-2-propyn-1-one;    -   2,5-heptadiyn-4-one/1-phenyl-2-propyn-1-one;    -   1-(p-methoxyphenyl)-2-propyn-1-one/1-phenyl-2-propyn-1-one;    -   1,4-diphenyl-2-butyn-1,4-dione/1-phenyl-2-propyn-1-one;    -   4,7-undecadiyn-6-one/1-phenyl-2-propyn-1-one;    -   1-(2-furyl)-3-phenyl-2-propyn-1-one/1-(2-furyl)-2-octyn-1-one;    -   1-octyn-3-one/1-(2-furyl)-2-octyn-1-one        1-(p-tolyl)-2-butyn-1-one;    -   2,5-heptadiyn-4-one/1-(2-furyl)-2-octyn-1-one;    -   1-(p-methoxyphenyl)-2-propyn-1-one/1-(2-furyl)-2-octyn-1-one;    -   1,4-diphenyl-2-butyn-1,4-dione/1-(2-furyl)-2-octyn-1-one;    -   4,7-undecadiyn-6-one/1-(2-furyl)-2-octyn-1-one;    -   1-octyn-3-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;    -   1-(p-tolyl)-2-butyn-1-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;    -   2,5-heptadiyn-4-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;    -   1-(p-methoxyphenyl)-2-propyn-1-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;    -   1,4-diphenyl-2-butyn-1,4-dione/1-(2-furyl)-3-phenyl-2-propyn-1-one;    -   4,7-undecadiyn-6-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;    -   1-(p-tolyl)-2-butyn-1-one/1-octyn-3-one;    -   2,5-heptadiyn-4-one/1-octyn-3-one;    -   1-(p-methoxyphenyl)-2-propyn-1-one/1-octyn-3-one;    -   1,4-diphenyl-2-butyn-1,4-dione/1-octyn-3-one;    -   4,7-undecadiyn-6-one/1-octyn-3-one;    -   2,5-heptadiyn-4-one/1-(p-tolyl)-2-butyn-1-one;    -   1-(p-methoxyphenyl)-2-propyn-1-one/1-(p-tolyl)-2-butyn-1-one;    -   1,4-diphenyl-2-butyn-1,4-dione/1-(p-tolyl)-2-butyn-1-one;    -   4,7-undecadiyn-6-one/1-(p-tolyl)-2-butyn-1-one;    -   1-(p-methoxyphenyl)-2-propyn-1-one/2,5-heptadiyn-4-one;    -   1,4-diphenyl-2-butyn-1,4-dione/2,5-heptadiyn-4-one;    -   4,7-undecadiyn-6-one/2,5-heptadiyn-4-one;    -   1,4-diphenyl-2-butyn-1,4-dione/1-(p-methoxyphenyl)-2-propyn-1-one;    -   4,7-undecadiyn-6-one/1-(p-methoxyphenyl)-2-propyn-1-one;    -   4,7-undecadiyn-6-one/1,4-diphenyl-2-butyn-1,4-dione.

According to the invention, the compound of formula 1 can be present inthe composition in a quantity comprised between 0.1% and 40%,preferentially between 0.1% and 10%, of the total weight of thecomposition.

The compounds of formula 1 are known for their significant reactivitywith the thiols and the amines.

They are easily obtained by the usual chemical synthesis routes andparticularly

-   -   either by the action of an acid chloride on a sodium derivative        of an alkyne according to

R—COCl+NaC≡C—R₁→R—CO—C≡C—R₁

-   -   or by oxidation of a secondary alcohol precursor according to

R—CH(OH)—C≡C—R₁→R—CO—C≡C—R₁

-   -   or by direct oxidation of an alkyne according to

R—CH₂—C≡C—CH₂—R₁→R—CO—C≡C—CH₂—R₁/R—CH₂—C≡C—CO—R₁

According to a variant of the invention, the deodorant composition canmoreover comprise at least one aldehyde chosen from the acyclic andnon-terpenic aliphatic aldehydes, the non-terpenic alicyclic aldehydes,the terpenic aldehydes, the aliphatic aldehydes substituted by anaromatic group, the bifunctional aldehydes, the aldehydes possessing anon-aromatic unsaturation borne by the carbon in the alpha position ofthe aldehyde function, the aldehydes possessing an unsaturation in thealpha position of the aldehyde function conjugated with an aromatic ringand the aldehydes the function of which is borne by an aromatic ring. Inthis variant, the composition can comprise a mixture of two or morealdehydes.

According to another, preferred, variant of the invention, the deodorantcomposition can moreover comprise a mixture of at least one firstaldehyde (aldehyde of class A) chosen from the acyclic and non-terpenicaliphatic aldehydes, the non-terpenic alicyclic aldehydes, the terpenicaldehydes, the aliphatic aldehydes substituted by an aromatic group andthe bifunctional aldehydes and at least one second aldehyde (aldehyde ofclass B) chosen from the aldehydes possessing a non-aromaticunsaturation borne by the carbon in the alpha position of the aldehydefunction, the aldehydes possessing an unsaturation in the alpha positionof the aldehyde function conjugated with an aromatic ring and thealdehydes the function of which is borne by an aromatic ring. In thisvariant, the composition can comprise a mixture of at least one firstand at least one second aldehyde. But the first aldehyde can of coursebe a mixture of two or more aldehydes of class A and the second aldehydecan be a mixture of two or more aldehydes chosen from those of class B.

According to the invention, the aldehydes of class A or B can be chosenfrom the natural or synthetic aldehydes, particularly from those classeswhich are not dangerous to the environment according to the EuropeanDangerous Substances Directive, authorized in food (FEMA No.) and inperfumery by the IFRA.

According to the invention, the acyclic and non-terpenic aliphaticaldehyde of class A can be chosen from

-   -   decanal;    -   undecanal;    -   dodecanal;    -   10-undecenal;    -   2-methyl undecanal;    -   trimethyl-2,6,10-undecen-9-al (ADOXAL™); or also    -   tetramethyl-2,3,5,5-hexanal.

Also according to the invention, the non-terpenic alicyclic aldehyde ofclass A can be chosen from

-   -   2,4-dimethylcyclohex-3-en-1-carboxaldehyde,    -   1,2-dimethylcyclohex-3-en-1-carboxaldehyde,    -   3,5-dimethylcyclohex-3-en-1-carboxaldehyde,    -   2,4,6-trimethylcyclohex-3-en-1-carboxaldehyde (ISOCYCLOCITRAL™),    -   tricyclo[5.2.1.0(0.6)]decyliden-8)-4-butanal (DUPICAL™);    -   trimethyl-2,6,10-undecen-9 al (ADOXAL™);    -   (methyl-4-penten-3-yl)-4-cyclohex-3-en-3-yl-1-carboxaldehyde;    -   6-methyl-8-(1-methylethyl)bicyclo[2.2.2]-5-octen-2-carboxaldehyde        (MACEAL™); or also    -   8,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene-2-carboxaldehyde        (ALDEHYDE 111™);    -   5-methyl furfural;    -   1-methyl-4-(4-methylpentyl)cyclohex-3-en-1-carboxaldehyde;    -   3-(5-methyl-2-furyl)butanal,6,6-dimethylbicyclo[3.1.1]-2-heptenyl-2-propanal;    -   tricyclodecanylcarboxaldehyde; or also    -   butylcinnamaldehyde

Preferentially the non-terpenic alicyclic aldehyde (AliNT) of class Acan be chosen from

-   -   8,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene-2        carboxaldehyde (ALDEHYDE 111™);    -   5-methyl furfural;    -   1-methyl-4-(4-methylpentyl)cyclohex-3-en-1-carboxaldehyde;    -   3-(5-methyl-2-furyl)butanal,6,6-dimethylbicyclo[3.1.1]-2-heptenyl-2-propanal;    -   tricyclodecanylcarboxaldehyde; or also    -   butylcinnamaldehyde.

Also according to the invention, the terpenic aldehyde (Terp) of class Acan be chosen from

-   -   citronellal;    -   hydroxycitronnellal;    -   2,2,3-trimethyl-3-cyclopenten-1-acetaldehyde(α-campholenaldehyde);    -   p-menth-1-en-9-al(carvomenthenal);    -   7,7-dimethylbicyclo[3.1.1]hept-3-en-4-carboxaldehyde(myrtenal);        or also    -   2-isopropyl-5-methyl-2-hexenal(isodihydrolavandulal).

Preferentially according to the invention, the terpenic aldehyde can bechosen from

-   -   α-campholenaldehyde;    -   carvomenthenal;    -   myrtenal; or also    -   isodihydrolavandulal.

Also according to the invention, the aliphatic aldehyde of class Asubstituted by an aromatic group can be chosen from

-   -   2-methyl-3-(p-isopropylphenyl)propanal;    -   3-(4-tert-butylphenyl)butanal;    -   phenylacetaldehyde;    -   3-phenylpropanal;    -   2-phenylpropanal;    -   2-methyl-3-(p-methylphenyl)propanal;    -   helional™;    -   cyclamen aldehyde;    -   lilial;    -   canthoxal™; or also    -   phenylacetaldehyde.

Preferentially according to the invention, the aliphatic aldehydesubstituted by an aromatic group can be chosen from

-   -   2-methyl-3-(p-isopropylphenyl)propanal;    -   3-(4-tert-butylphenyl)butanal;    -   phenylacetaldehyde;    -   3-phenylpropanal;    -   2-phenylpropanal; or also    -   2-methyl-3-(p-methylphenyl)propanal.

By “bifunctional aldehyde”, is meant according to the invention thealdehydes also possessing another function such as for example anether-oxide or alcohol function. The bifunctional aldehyde can accordingto the invention be chosen from

-   -   the alkoxy-acetaldehydes;    -   the hydroxy-aldehydes;    -   the alkoxy-aldehydes;        such as for example    -   3 and 4-(4-hydroxy-4-methylpentyl)-3-cyclohexen-1-carboxaldehyde        (LYRAL™);    -   methoxydicyclopentadiencarboxaldehyde;    -   3-(1,3-benzodioxol-5-yl)-2-methylpropanal; or also    -   7-hydroxy-3,7-dimethyloctanal(hydroxycitronellal).

Preferentially according to the invention, the bifunctional aldehyde canbe

-   -   methoxydicyclopentadiencarboxaldehyde; or also    -   7-hydroxy-3,7-dimethyloctanal.

According to the invention, the aldehyde which possesses an unsaturationof non-aromatic type (class B) borne by the carbon in the alpha positionof the aldehyde function can be chosen from

-   -   citral (neral and geranial);    -   myrtenal;    -   perillaldehyde;    -   furyl-2-carboxaldehydes substituted or unsubstituted,        preferentially those unsubstituted or substituted by at least        one methyl;    -   2,4-heptadienal;    -   2E,4E-undecadienal;    -   2E,4E-dodecadienal;    -   2E-decenal;    -   2E,4Z,7Z-tridecatrienal;    -   2E,6Z-nonadienal;    -   2-furfurylidenebutanal;    -   3,7-dimethyl-2-methylen-6-octenal; or also    -   2E-dodecenal.

Preferentially according to the invention, the aldehyde which possessesan unsaturation of non-aromatic type (class B) borne by the carbon inthe alpha position of the aldehyde function can be

-   -   citral;    -   myrtenal;    -   perillaldehyde;    -   2E-dodecenal; or also    -   2-furfurylidenebutanal.

The aldehyde (of class B) which possesses an ethylenic unsaturation inthe alpha position, conjugated with an aromatic ring can be chosen from

-   -   cinnamaldhyde;    -   α-amylcinnamaldehyde (JASMONAL™);    -   α-hexylcinnamaldehyde;    -   (E)-3-(2-methoxyphenyl)prop-2-enal;    -   (E)-3-(4-methoxyphenyl)prop-2-enal;    -   α-methylcinnamaldehyde;    -   1-benzofuran-2-carboxaldehyde;    -   2-phenyl-2-butenal; or also    -   5-methyl-2-phenyl-2-hexenal.

Preferentially according to the invention, the aldehyde which possessesan ethylenic unsaturation in the alpha position, conjugated with anaromatic ring can be

-   -   (E)-3-(2-methoxyphenyl)prop-2-enal;    -   (E)-3-(4-methoxyphenyl)prop-2-enal;    -   1-benzofuran-2-carboxaldehyde;    -   2-phenyl-2-butenal; or also    -   5-methyl-2-phenyl-2-hexenal.

The aldehyde borne by an aromatic ring, itself optionally substitutedmoreover, can be chosen from

-   -   vanilline;    -   ethylvanilline;    -   vanillyl acetate;    -   benzaldehyde;    -   anisaldehyde.    -   cinnamaldhyde;    -   α-amylcinnamaldehyde (JASMONAL™);    -   α-hexylcinnamaldehyde;    -   (E)-3-(2-methoxyphenyl)prop-2-enal;    -   (E)-3-(4-methoxyphenyl)prop-2-enal;    -   α-methylcinnamaldehyde;    -   1-benzofuran-2-carboxaldehyde;    -   2-phenyl-2-butenal; or also    -   5-methyl-2-phenyl-2-hexenal.

Preferentially according to the invention, the aldehyde borne by anaromatic ring, itself optionally substituted moreover, can be chosenfrom

-   -   vanilline;    -   ethylvanilline;    -   vanillyl acetate;    -   benzaldehyde; or also    -   anisaldehyde.

Under preferential conditions for implementation of the second variantof the invention described above, the first aldehyde can be chosenpreferably from the acyclic and non-terpenic aliphatic aldehydes, thenon-terpenic alicyclic aldehydes, the terpenic aldehydes and thealiphatic aldehydes substituted by an aromatic group, the secondaldehyde can be chosen preferably from the aldehydes which possess anunsaturation of non-aromatic type borne by the alpha carbon.

Quite particularly, the first aldehyde can be chosen from the aliphaticor acyclic and non-terpenic aliphatic aldehydes and the second from theterpenic aldehydes possessing an unsaturation on the alpha carbonreferred to above.

Particularly useful pairs of aldehydes can be chosen in particular fromthe following pairs, without any limitation:

-   -   dodecanal and myrtenal;    -   dodecanal and citral;    -   adoxal and perillaldehyde;    -   triplal and citral;    -   maceal and citral;    -   adoxal and myrtenal;    -   decanal and citral; or also    -   10-undecenal and myrtenal.

According to the first variant of the invention the composition cancomprise the aldehyde in a quantity comprised between 0.5% and 50% ofthe composition, preferentially in a quantity comprised between 1% and20% of the composition.

According to the second variant of the invention the composition cancomprise the aldehydes of classes A and B in proportions relative toeach other, in proportions from 80/20 to 20/80 in particular inproportions of 50/50 and in a total quantity of aldehydes comprisedbetween 1% and 90% of the composition, preferentially in a quantitycomprised between 10% and 30% of the composition.

The deodorant compositions according to the invention, in addition totheir remarkable deodorant properties, also themselves possess odiferousproperties optionally capable of replacing unpleasant odours with theirown odour.

According to yet another variant of the invention the deodorantcompositions can moreover comprise a masking agent.

These compositions can therefore comprise at least one odoriferous agentsuch as those conventionally used in perfumery such as alcohols,essential oils, phenolic substances, esters.

These deodorant compositions are used under all conditions where it issought to combat unpleasant odours, of whatever origin.

The compositions according to the invention can also contain specificsubstances, such as for example bactericides.

These deodorant compositions are advantageously formulated according tothe usual techniques.

This is why a subject of the present Application is also deodorantproducts characterized in that they contain the compositions describedabove.

These products can be presented in the form of aerosol sprays,impregnated solid supports, liquids, cremes, powders, etc. They can beproduced according to the methods known to a person skilled in the art.

A subject of the invention is also the use of a compound of the familyof acetylenic ketones corresponding to formula 1 in a deodorantcomposition, particularly in deodorant compositions comprising at leastone aldehyde chosen from the acyclic and non-terpenic aliphaticaldehydes, the non-terpenic alicyclic aldehydes, the terpenic aldehydes,the aliphatic aldehydes substituted by an aromatic group, thebifunctional aldehydes, the aldehydes possessing a non-aromaticunsaturation borne by the carbon in the alpha position of the aldehydefunction, the aldehydes possessing an unsaturation in the alpha positionof the aldehyde function conjugated with an aromatic ring and thealdehydes the function of which is borne by an aromatic ring, and evenmore preferentially in a deodorant composition comprising a mixture ofat least one first aldehyde (aldehyde of class A) chosen from theacyclic and non-terpenic aliphatic aldehydes, the non-terpenic alicyclicaldehydes, the terpenic aldehydes, the aliphatic aldehydes substitutedby an aromatic group and the bifunctional aldehydes and at least onesecond aldehyde (aldehyde of class B) chosen from the aldehydespossessing a non-aromatic unsaturation borne by the carbon in the alphaposition of the aldehyde function, the aldehydes possessing anunsaturation in the alpha position of the aldehyde function conjugatedwith an aromatic ring and the aldehydes the function of which is borneby an aromatic ring.

Other advantages, aims and characteristics may become apparent from thedescription which follows, given by way of explanation and in no waylimitative, of the attached drawings in which:

FIG. 1 illustrates the degradation of butylamine under the effect ofα-acetylenic ketones according to the invention.

FIG. 2 illustrates the degradation of butylamine under the effect of aknown neutralizing agent to which an α-acetylenic ketone according tothe invention is added.

EXPERIMENTAL PART

The examples which follow illustrate the present invention, withouthowever limiting it.

Preparation of the α-acetylenic ketones I—Disubstituted acetylenicketones R—CO—C≡C—R₁ 1.1 Preparation of 4-decyn-3-one (Inert Atmosphere)

A 1-litre reactor was loaded with 345 mL of diglyme (RN 111-96-6) and17.2 g (748 mmoles) of sodium (RN 7440-23-5) cut into pieces. Afterheating to a temperature slightly above the melting point of sodiumaccompanied by thorough stirring, 71.7 g (745 mmoles) i.e. 97.5 mL of1-heptyne (RN 628-71-7) in solution in 100 mL of diglyme is then addedfour times at hourly intervals. The medium thickens to form a beigesuspension. Stirring is continued for another 2 hours 30 minutes at thesame temperature. The mixture is cooled down to 25-30° C. and pouredslowly into a stirred solution of 64.8 g (700 mmoles) i.e. 61.0 mL ofpropionyl chloride (RN 79-03-8) in 600 mL of ethyl ether. An exothermicreaction takes place followed by stirring for 1 hour at no particulartemperature.

After washing with 4×1 litre of water, drying and concentration underreduced pressure (25 mm Hg) 98 g of a orange-yellow liquid is obtained.The latter is fractionated under reduced pressure (2 mm Hg). Thefraction the temperature of which passes 70-71° C. is collected. Yield50 g i.e. 47%.

5-decyn-4-one, 3-octyn-2-one, 4-phenyl-3-butyn-2-one, 9-hexadecyn-8-one,1-(2-furyl)-3-phenyl-2-propyne-1-one and 1-cyclopentyl-4-nonyn-3-one(non-limitative examples) are prepared analogously.

1.11 Preparation of the Mixture of 4-nonyn-3-one and 5-nonyn-4-one

A 500-mL reactor is loaded with 13.8 g (111 mmoles) of 4-nonyne (RN20184-91-2), 175 mL of tert-butanol (RN 75-65-0), 770 mg (4.5 mmoles) ofcupric chloride dihydrate (RN 10125-13-0), and 33.4 mL (244 mmoles) of70% tert-butyl hydroperoxide (RN 75-91-2). Accompanied by thoroughstirring and under an atmosphere of pure oxygen originating from agraduated tank, the medium is heated to 60-65° C. At the end of threehours it is noted that the medium absorbs no more oxygen and hasconsumed the theoretical quantity.

The medium is poured over ice and extracted three times with ether. Thecombined organic phases are washed four times with 5% saltwater. Afterdrying and concentration approximately 40 g of a green liquid isobtained, which is fractionated by distillation under reduced pressure(20 mm Hg). The two isomers, which are not separated, distill togetherbetween 92 and 97° C.

2-methyl-5-decyn-4-one and 9-methyl-5-decyn-4-one as well as1-phenyl-1-pentyn-3-one (the latter in a single isomer, a single site ofthe starting 1-phenyl-1-pentyne being able to be oxidized) are preparedanalogously.

II—True acetylenic ketones R—CO—C≡CH, Disubstituted acetylenic ketonesR—CO—C♭C—R1 IIA—Preparation of 1-octyn-3-one IIA-1) Preparation of1-octyn-3-ol (Inert Atmosphere)

A 750-mL reactor is loaded with 40.1 g (400 mmoles) i.e. 49.2 mL ofhexanal (RN 66-25-1) and 400 mL of anhydrous tetrahydrofuran and 100 gof a suspension of 18% sodium acetylide (RN 1066-26-8) in xylene (375mmoles) is added by portions accompanied by stirring. An exothermicreaction takes place. Stirring is then continued for another 2 hours atno particular temperature. After hydrolysis, extractions andconcentration, fractionation is carried out under reduced pressure.

It is however to be noted that a better result is obtained by usingethynylmagnesium bromide (RN 4301-14-8). This is for example the casewith 1-decyn-3-ol.

IIA-2) Preparation of 1-octyn-3-one

A 1500-mL reactor is loaded with 25.24 g (200 mmoles) i.e. 29.1 mL of1-octyn-3-ol, 600 mL of acetone and 90 mL of water. Accompanied byvigorous stirring a solution of 29.4 g (100 mmoles) of potassiumdichromate of (RN 7778-50-9) in 300 mL of water and 22 mL of sulphuricacid is added over 1 hour 30 minutes. The coloration changes from orangeto green. At the end, stirring is continued for another 30 minutes then1000 mL of water is added also over 30 minutes.

After extractions with ethyl ether, washings, drying and concentrationunder slightly reduced pressure, 25 g of an orange liquid is obtained,which is fractionated under reduced pressure (20 mm Hg). The fractionthe temperature of which passes 74-76° C. is collected.

1-phenyl-2-propyn-1-one and 1-decyn-3-one and1-(p-methoxyphenyl)-2-propyn-1-one are prepared analogously.

IIA-3 Other Preparations

1-cyclohexyl-4-ethyl-1-hexyn-3-one, 7-tetradecyn-8-one, 2-nonyn-4-one,9-hexadecyn-8-one and 1-(p-tolyl)-2-butyn-1-one are preparedanalogously, using the salt of a substituted alkyne (Na—C≡C—R).

III—Evaluation of the Effect of the Compositions According to theInvention on Unpleasant Odours

Organoleptic tests, with formulae containing or not containingacetylenic ketones described previously record significant reduction ofcomplex unpleasant odours (cooking, toilet, tobacco odours).

III-1 Protocol

The olfactory test is carried out with a panel of 25 experts.

The α-acetylenic ketones to be tested are prepared at a concentration of1 mol/L in dipropylene glycol.

The reference malodorous solution is also prepared at a concentration of1 mol/L.

A first pillbox contains 1 g of the reference malodorous solution.

An equimolar mixture of 1 g of a solution of α-acetylenic ketone and 1 gof solution of reference malodorous solution is placed in otherpillboxes (1 pillbox per α-acetylenic ketone to be tested).

The unpleasant odour released by the first pillbox is assigned thereference 10 (reference malodorous solution).

Using a Latin square (table indicating the order to be followed by eachjudge in the testing panel in order to avoid bias), the other pillboxesare evaluated in comparison with the first.

The results are then converted to percentages of residual unpleasantodour.

The following α-acetylenic ketones are tested on different solutions ofreference malodorous solution:

-   -   A: 6-phenyl-5-hexyn-2,4-dione of formula C₆H₅—C≡C—CO—CH₂—CO—CH₃;    -   B: 4-phenyl-3-butyn-2-one of formula C₆H₅—C≡C—CO—CH₃;    -   C: 2-decen-5-yn-4-one of formula C₄H₉—C≡C—CO—CH═CH—CH₃;    -   D: 7-tetradecyn-6-one of formula C₆H₁₃—C≡C—CO—O₅H₁₁

III-2 Test of Effectiveness on butylamine

% of residual unpleasant odour 1 g of butylamine (Reference) 100 1 g ofbutylamine + 1 g of A 30 1 g of butylamine + 1 g of B 28 1 g ofbutylamine + 1 g of C 25 1 g of butylamine + 1 g of D 58

A clear reduction in the residual odour is noted

III-3 Test of Effectiveness on thioglycolic Acid

% of residual unpleasant odour 1 g of acid thioglycolic (Reference) 1001 g of acid thioglycolic + 1 g of A 57 1 g of acid thioglycolic + 1 g ofB 30 1 g of acid thioglycolic + 1 g of C 57 1 g of acid thioglycolic + 1g of D 49

A clear reduction in the residual odour is noted

III—Test of Effectiveness on an Unpleasant Cooking Odour

This test aims to show the potentiating effect of the α-acetylenicketones on an already known deodorant, Neutral 1.

An unpleasant cooking odour is prepared by mixing the followingdifferent compounds:

Compound % in the mixture Characteristic odour Trimethylamine 0.10 FishDimethyl sulphide 0.13 Cabbage Dimethyl disulphide 0.02 Onion Pyridine,2-methanethiol 0.50 Rotten meat 10% Isovaleric acid 0.70 Sweat, CheeseButyric acid 0.30 Cheese Capric acid 0.50 Fermented Cheese Methyl amylketone 0.10 Strong blue cheese 2-Mercaptopropanone 0.06 Meat,Sulphuousr, Mould Diallyl disulphide 0.05 Garlic Butyl butyryllactate1.30 Sour milk Methional 0.02 Old potato Indole 1% 0.14 Rottenvegetable, mould Diacetyl 0.10 Rancid butter Hexanoic acid 0.20 Oldcheese Guaiacol 0.04 Cooked meat Propylene glycol 95.74 Support

20 μL of this unpleasant odour is deposited on a 1 cm² cellulosesupport, which is placed in a 3 m³ odour chamber. This enclosure servesas a reference.

In the same way, identical closed enclosures containing the unpleasantodour to which 10 μL of Neutral 1 alone, i.e. 10 μL of a mixture ofNeutral and of an α-acetylenic ketone (in a proportion of 99/1) are alsoprepared.

The testing panel then evaluates the odour in each of the enclosures,according to the order defined by a Latin square and in comparison withthe reference enclosure containing the unpleasant odour alone.

The following α-acetylenic ketones are tested on the referencemalodorous solution:

-   -   E: Neutral 1    -   F: Neutral 1 and 2,2-dimethyl-4-hexyn-3-one of formula        CH₃—C≡C—CO—C(CH₃)₃    -   G: Neutral 1 and 5-decyn-4-one of formula C₄H₉—C≡C—CO—C₃H₇    -   H: Neutral 1 and 2,5-heptadiyn-4-one of formula        H₃C—C≡C—CO—C≡C—CH₃    -   I: Neutral 1 and 3-octyn-2-one of formula C₄H₉—C≡C—CO—CH₃

Formula of Neutral 1:

Compound Quantity (vol./vol.) Phenylacetaldehyde (A) 0.32%Hydroxycitronellal (A) 1.63% α-Hexylcinnamaldehyde (B) 19.09% Lilial (A)7.91% DiPropyleneGlycol qsf 100

% of residual unpleasant odour Cooking odour 100 alone (OdC = Reference)OdC + E 39 OdC + F 32 OdC + G 24 OdC + H 30 OdC + I 36

The addition of a small of α-acetylenic ketone in addition to theNeutral improves the effectiveness of Neutral 1 against the unpleasantcooking odour.

III-5 Test of Effectiveness on an Unpleasant Tobacco Odour

An unpleasant tobacco odour is prepared from ash and cigarette ends. 20g of this odour is deposited in a 3 m³ odour chamber.

Cloth towels are deposited in the enclosure and left for 24 hours inorder to become impregnated with the tobacco odour.

100 μL of Neutral 2 is then sprayed on the linen cloth.

Similarly towels brought into contact with the tobacco odour areprepared and mixtures of anti-tobacco Neutral 2 and a small α-acetylenicketone (in a proportion of 99/1) or a mixture of two small α-acetylenicketones (in a proportion of 99/0.5/0.5) are sprayed on the towels.

The panel then evaluates the quantity of unpleasant tobacco odour on thetowels in comparison with towels which had received no treatment againstthe unpleasant odour.

The following α-acetylenic ketones are tested on the referencemalodorous solution:

-   -   J: Neutral 2,    -   K: Neutral 2 and 2,5-heptadiyn-4-one of formula        H₃C—C≡C—CO—C≡C—CH₃,    -   L: Neutral 2 and 1-octyn-3-one of formula C₅H₁₁—CO—C≡CH,    -   M: Neutral 2 and 5-decyn-4-one of formula C₄H₉—C≡C—CO—C₃H₇,    -   N: Neutral 2 and 1-phenyl-2-propyn-1-one of formula        C₆H₅—CO—C≡CH, and 6-phenyl-5-hexyn-2,4-dione of formula        C₆H₅—C≡C—CO—CH₂—CO—CH₃,    -   O: Neutral 2 and 4-phenyl-3-butyne-2-one of formula        C₆H₅—C≡C—CO—CH₃, and 1-phenyl-2-propyn-1-one of formula        C₆H₅—CO—C≡CH,

Formula of Neutral 2:

Compound Quantity (vol./vol.) Lilial (A) 10% Anisaldehyde 20%α-Hexylcinnamaldehyde (B) 69% Butylhydroxytoluene qsf 100

Spray formula:

Compound Quantity (v/v) Ethyl alcohol 15.0 Sodium lauroyl sarcosinate0.5 Sodium carbonate 2.0 Sodium dioctyl sulphosuccinate 0.5 Neutral 20.5 Demineralized water qsf 100

% of residual unpleasant odour Tobacco odour 100 alone (OdT = Reference)OdT + J 65 OdT + K 33 OdT + L 39 OdT + M 51 OdT + N 51 OdT + O 55

The effectiveness of Neutral 2 is improved by the addition of at leastone α-acetylenic ketone.

III-6 Test of Effectiveness on an Unpleasant Toilet Odour

An unpleasant toilet odour is prepared by mixing the following differentcompounds:

Compound % in the mixture Characteristic odour Scatole 0.90 FaecalThionaphthol 0.90 Faecal, sulphurous Thioglycolic acid 21.18 SulphurousHexanoic acid 6.00 Sweat p-Cresyl isovalerate 2.18 Faecal, sweatN-Methyl morpholine 6.00 Urine Dipropylene Glycol (DPG) qsf 100

20 μL of this unpleasant odour is deposited in the water of a toiletbowl in a cubicle. 20 μL of unpleasant odour as well as 20 μL of aNeutral 3 which is active against the unpleasant toilet odour aredeposited in another cubicle.

In other cubicles, an α-acetylenic ketone in a proportion of 99/1 withNeutral 3 is added in addition.

The quantity of unpleasant toilet odour in each cubicle is thenevaluated by the testing panel.

The following α-acetylenic ketones are tested on the referencemalodorous solution:

-   -   P: Neutral 3;    -   Q: Neutral 3 and 2,5-heptadiyn-4-one of formula        H₃C—C≡C—CO—C≡C—CH₃;    -   R: Neutral 3 and 2,2-dimethyl-4-hexyn-3-one of formula        CH₃—C≡C—CO—C(CH₃)₃;    -   S: Neutral 3 and 1-octyn-3-one of formula C₅H₁₁—CO—C≡CH;    -   T: Neutral 3 and 5-decyn-4-one of formula C₄H₉—C≡C—CO—C₃H₇;

Formula of Neutral 3:

Compound Quantity (vol./vol.) Citral 3.5% Orange terpenes 1.5% LinalylAcetate 11.0% Linalol 23.0% Citral DEA 0.3% Eugenol 5.0% 3Z-hexenylacetate 10% DPG 5.0% α-hexyl cinnamic aldehyde 15.0% Hederile 10% DPG1.0% Butylhydroxytoluene 10% DPG 0.2% Dipropylene Glycol (DPG) qsf 100%

% of residual unpleasant odour Toilet odour alone (OdT = Reference) 100OdT + P 47 OdT + Q 19 OdT + R 20 OdT + S 21 OdT + T 23

The effectiveness of Neutral 3 is improved by the addition of at leastone α-acetylenic ketone.

IV—Chemical Reactivity

Parallel tests contribute to recording the reactivity of theketo-alkynes. They are carried out by a mole to mole reaction of aketo-alkyne with a substance responsible for an unpleasant odour. Thereaction is carried out at ambient temperature in THF.

40 acetylenic ketones are tested in order to verify their reactivity(their potential to reduce unpleasant odours).

IV-1 Reactivity with piperidine

A substrate, piperidine, is used to verify this reactivity. Thereactivity is measured by the signal obtained in gaseous phasechromatography (respective signal obtained after a reaction time t=5min, t=2 hours and t=5 hours measured for the keto-alkyne, for thereaction product).

IV-1.1 Reaction Time 5 Minutes

Compounds t = 5 min C₆H₅—CO—C≡CH 0 CH₃—C≡C—CO—C≡C—CH₃ 0CH₃O—C₆H₄—CO—C≡CH 0 C₆H₅—C≡C—CO—C₄H₃O (furyl) 0 C₃H₇—C≡C—CO—C≡C—C₃H₇ 0C₆H₅—CO—C≡C—CO—C₆H₅ 1 C₇H₁₅—CO—C≡CH 4 C₅H₁₁—C≡C—CO—C₄H₃O (furyl) 5C₅H₁₁—CO—C≡CH 8 CH₃—C≡C—CO—C₆H₄—(p-CH₃) 9

Five acetylenic ketones show a very strong reactivity vis-à-vis thesubstrate used. 5 min after the two reagents are brought into contact,the keto-alkyne has totally disappeared and the formation of thereaction substance reaches its maximum.

Five other acetylenic ketones show a strong reactivity with a 90 to 99%disappearance of the reagents after 5 minutes.

IV-1.2 Reaction Time 2 Hours

Examination of the reactivity after reaction for 2 hours shows thedisappearance of more than 90% of the acetylenic ketones (and theappearance of the reaction product) with more than half of the productstested (24 out of 40).

t = 2 Compounds hours C₆H₅—CO—C≡CH 0 CH₃—C≡C—CO—C≡C—CH₃ 0CH₃O—C₆H₄—CO—C≡CH 0 C₅H₁₁—C≡C—CO—C₄H₃O (furyl) 0 CH₃—C≡C—CO—C₆H₃(OCH₃)₂0 C₆H₅—CO—C≡C—CO—C₆H₅ 0 C₃H₅—C≡C—CO—C₆H₄—CH₃ 0 C₆H₅—C≡C—CO—C₄H₃O (furyl)0 CH₃—C≡C—CO—C₆H₄—(p-CH₃) 0 C₃H₇—C≡C—CO—C≡C—C₃H₇ 0C₂H₅—CO—C≡C—(CH₂)₄—C≡C—CO—C₂H₅ 1 C₆H₅—C≡C—CO—C₂H₅ 1C₆H₅—C≡C—CO—CH₂—CO—CH₃ 2 C₆H₅—C≡C—CO—CH₃ 2 CH₃—C≡C—CO—C(CH₃)₃ 2CH₃—C≡C—CO—C₅H₁₁ 4 C₇H₁₅—CO—C≡CH 4 C₃H₇—CH₂—C≡C—CO—CH(CH₃)₂ 5C₃H₇—CO—C≡C—CH₂—CH(CH₃)₂ C₅H₁₁—CO—C≡CH 7 C₆H₅—C≡C—CO—C₄H₉ 7C₃H₅—C≡C—CO—CH(C₂H₅)—C₄H₉ 8 (CH₃)₂CH—C₂H₄—C≡C—CO—CH₂—CH(CH₃)₂ 8C₅H₁₁—C≡C—CO—C₂H₅ 9 C₆H₁₃—C≡C—CO—C₇H₁₅ 9

IV-1.3 Reaction Time 5 Hours

Examination of the reactivity after reaction for 5 hours shows thedisappearance of more than 90% of the acetylenic ketones (and theappearance of the reaction product) with virtually all of the productstested (36 out of 40).

Three acetylenic ketones react strongly with a disappearance of 55 to83%. Only one substance shows no reactivity.

Compounds t = 5 hours CH₃—C≡C—CO—C(CH₃)₃ 0 CH₃—C≡C—CO—C≡C—CH₃ 0CH₃O—C₆H₄—CO—C≡CH 0 C₅H₁₁—C≡C—CO—C₄H₃O (furyl) 0 CH₃—C≡C—CO—C₆H₃(OCH₃)₂0 C₆H₅—CO—C≡C—CO—C₆H₅ 0 C₃H₅—C≡C—CO—C₆H₄—(p-CH₃) 0 C₆H₅—C≡C—CO—C₄H₃O(furyl) 0 CH₃—C≡C—CO—C₆H₄—(p-CH₃) 0 C₃H₇—C≡C—CO—C≡C—C₃H₇ 0C₂H₅—CO—C≡C—(CH₂)₄—C≡C—CO—C₂H₅ 0 C₆H₅—CO—C≡CH 0 C₆H₅—C≡C—CO—CH₃ 0C₅H₁₁—C≡C—CO—C₂H₅ 1 C₃H₅—C≡C—CO—CH(C₂H₅)—C₄H₉ 1 C₆H₁₃—C≡C—CO—C₇H₁₅ 1CH₃—C≡C—CO—C₅H₁₁ 1 C₆H₅—C≡C—CO—CH₂—CO—CH₃ 1 C₆H₅—C≡C—CO—C₂H₅ 1C₆H₁₃—C≡C—CO—C₅H₁₁ 2 C₄H₉—C≡C—CO—CH₃ 2 C₂H₅—CO—C≡C₆(CH₂)₄—C≡CH 2C₄H₉—C≡C—CO—(CH₂)₂—C₅H₉ 3 C₃H₇—C≡C—CO—C₄H₉ 3 C₃H₇—CH₂—C≡C—CO—CH(CH₃)₂ 4C₃H₇—CO—C≡C—CH₂—CH(CH₃)₂ C₇H₁₅—CO—C≡CH 4 C₃H₇—C≡C—CO—CH(CH₃)₂ 6C₄H₉—C≡C—CO—C₃H₇ 6 C₄H₉—C≡C—CO—C₃H₅ (cyclopropyl) 7(CH₃)₂CH—C₂H₄—C≡C—CO—CH₂—CH(CH₃)₂ 7 C₆H₅—C≡C—CO—C₄H₉ 7 C₅H₁₁—CO—C≡CH 8C₄H₉—C≡C—CO—C₆H₁₁ 8 (CH₃)₂CH—C₂H4—C≡C—CO—C(CH₃)₃ 9 C₃H₇—CH₂—C≡C—CO—C₂H₅10 C₃H₇—CO—C≡C—CH₂—C₂H₅ C₄H₉—C≡C—CO—CH═CH—CH₃ 17(CH₃)₂CH—C₂H₄—C≡C—CO—CH(C₂H₅)—C₄H₉ 23 C₆H₁₁—C≡C—CO—CH(C₂H₅)₂ 45(CH₃)₂CH—CO—C≡C—CH₂—O—CH₂—C≡C—CO—CH(CH₃)₂ 87

IV-2 Reactivity with the mercaptans

Three sulphurous compounds serve as support for the reactivity of theacetylenic ketones (butanethiol, 2-phenylethanethiol andα-toluenethiol).

Five acetylenic ketones which reacted strongly with piperidine weretested.

The operating conditions are identical to those previously described forpiperidine (Mole to mole reaction of a keto-alkyne with a mercaptan).

The reaction is carried out at ambient temperature in THF.

The reactivity is monitored by chromatographic measurements which arecarried out for 3 hours after the following reaction times:

t=5 min, t=40 min, t=75 min, t=110 min, t=145 min, t=180 min.

IV-2.1. Reactivity with 2-phenylethanethiol

Concentration of the acetylenic ketones (% GC) Time (minutes) 5 40 75110 145 180 C₆H₅—CO—C≡CH 3 — — — — — CH₃O—C₆H₄—CO—C≡CH 6 — — — — —CH₃—C≡C—CO—C≡C—CH₃ 90 20  2 — — — C₆H₅—C≡C—CO—C₄H₃O (furyl) 88 35 24 13— — C₃H₇—C≡C—CO—C≡C—C₃H₇ 87 46 40 35 29 26

Two of these substances react instantaneously, two others disappearafter 2 hours of reaction, the fifth reacts strongly after only 3 hoursof reaction.

Three other acetylenic ketones, 1-cyclopentyl-4-nony-3-one,(C₄H₉—C≡C—CO—C₂H₄—C₅H₉), 1-cyclopropyl-2-heptyn-1-one (C₄H₉—C≡C—CO—C₃H₅)and 5-decyn-4-one (C₄H₉—C≡C—CO—C₃H₇) do not react with2-phenylethanethiol. The addition of a catalyst promotes theirreactivity very slightly.

IV-2.2. Reactivity with butanethiol

Concentration of the acetylenic ketones (% GC) Time (minutes) 5 40 75110 145 180 C₆H₅—CO—C≡CH 2 — — — — — CH₃O—C₆H₄—CO—C≡CH 12 tr — — — —CH₃—C≡C—CO—C≡C—CH₃ 78 14  6  2 — — C₆H₅—C≡C—CO—C₄H₃O (furyl) 95 82 67 5345 39 C₃H₇—C≡C—CO—C≡C—C₃H₇ 96 86 75 60 44 40

The reactivity with butanethiol is fairly similar to that of2-phenylethanethiol.

IV-2.3. Reactivity with toluenethiol

Concentration of the acetylenic ketones (% GC) Time (minutes) 5 40 75110 145 180 CH₃—C≡C—CO—C≡C—CH₃ 2 — — — — — C₆H₅—C≡C—CO—C₄H₃O (furyl) 16— — — — —

The reaction with toluenethiol is very rapid with two targets and slowerwith the three other targets tested.

V—Chromatographic Tests

Gas chromatography: use of an internal standard, ethyl decanoate.

The peaks corresponding to each α-acetylenic ketone, to butylamine, tothe internal standard and to the solvent are determined.

The surface areas of the peaks make it possible to determine theresidual quantity of butylamine (unpleasant odour).

Chromatographic analyses are carried out every 25 minutes in order toestablish kinetics.

The results are presented in FIG. 1.

Used alone in a proportion of 1/10 (α-acetylenic ketone/butylamine), theα-acetylenic ketones lead to a 4 to 8% reduction in the quantity ofbutylamine in less than 3 hours.

The effect of Neutral 2 alone on butylamine and the effect of Neutral 2to which 1% α-acetylenic ketone is added are tested in comparison withthe previous tests.

The results are presented in FIG. 2.

As increase in the effectiveness of Neutral 2 on the quantity ofbutylamine is noted.

The tests described in paragraphs IV and V demonstrate that theα-acetylenic ketones exert their deodorant effect by physicallydestroying the malodorous molecules. This effect is therefore not asimple masking effect.

VI—Deodorant Compositions VI-1. Aerosol Air Freshener

An aqueous air spray perfumed with a “magnolia” neutralizer containingthe following aldehydes:

Phenylacetaldehyde (A) 0.32% Hydroxycitronellal (A) 1.63%α-Hexylcinnamaldehyde (B) 19.09% Lilial (A) 7.91%2,4-Dimethyl-3-cyclohexen-1-carboxaldehyde (A) 0.15% DPG Qsf 100

VI-2. Deodorant and Disinfectant Liquid for Floors

The aldehydes can also be formulated in the form of acetals in order toreduce the intrinsic odour of the neutralizer and increase the durationof action. It is known that an acetal is hydrolyzed in acid mediumreleasing the corresponding aldehyde.

By way of examples, here are a few acetals with a faint odour which canbe used in a surface deodorant: propionaldehyde DEA,phenylacetaldehyde-methanol acetal, citral diethylacetal,hydroxycitronnellal dimethylacetal, benzaldehyde diethylacetal.

Surface Deodorant Formula:

Compound Quantity (v/v) Ethyl alcohol 15.0 Sodium lauroyl sarcosinate0.5 Sodium carbonate 2.0 Sodium dioctyl sulphosuccinate 0.5 Neutral 20.5 Demineralized water qsf 100

1-26. (canceled)
 27. A method for destroying malodorous molecules usinga deodorant composition, wherein said deodorant composition comprises atleast one compound of the family of the α-acetylenic ketonescorresponding to general formula 1R—(CO)_(k)—C≡C-(A)-(C≡C)_(m)—(CO)_(n)—R₁   (1) in which R and R₁ canrepresent, independently or simultaneously, a radical selected from thegroup consisting of an alkyl chain comprising from 1 to 9,preferentially from 3 to 7 carbon atoms, linear or branched, substitutedor unsubstituted, a cycloalkane comprising from 3 to 8, preferentiallyfrom 5 or 6 carbon atoms, substituted or unsubstituted; a furan ring,saturated or unsaturated, substituted or unsubstituted; a pyran ring,saturated or unsaturated, substituted or unsubstituted; an aromatic ringcomprising from 6 to 8 carbon atoms, substituted or unsubstituted; and ahydrogen atom, A represents a group selected from the group consistingof —(CH₂)_(x) with x representing an integer with a value from 0 to 6,preferentially from 0 to 4, (—CO)₁ with 1 representing an integer with avalue of 0 or 1, or also a (CH₂)_(y)—O—(CH₂)_(z)— chain formation with yand z representing, simultaneously or independently, an integer with avalue from 0 to 6, preferentially from 0 to 4, wherein x+y does notexceed the value of 6; k, m and n are, simultaneously or independently,an integer with a value of 0 or 1, wherein k and n do not simultaneouslyhave a value of 0 if 1 is equal to 0; with the exception of2-methyl-4-nonyn-3-one of formula C₄H₉—C≡C—CO—CH(CH₃)₂ in a deodorantcomposition.
 28. The method of claim 27, wherein the compound of formula1 is selected from the group consisting of 1-octyn-3-one of formulaC₅H₁₁—CO—C≡CH; 3-octyn-2-one of formula C₄H₉—C≡C—CO—CH_(3;) 4-octyn3-one of formula C₃H₇—C≡C—CO—C₂H₅; 4-nonyn-3-one of formulaC₃H₇—CH₂—C≡C—CO—C₂H₅; 2-nonyn-4-one of formula CH₃—C≡C—CO—C₅H₁₁;5-nonyn-4-one of formula C₃H₇—CO—C≡C—CH₂—C₂H₅; 1-decyn-3-one of formulaC₇H₁₅—CO—C≡CH; 4-decyn-3-one of formula C₅H₁₁—C≡C—CO—C₂H_(5;)6-decyn-5-one of formula C₃H₇—C≡C—CO—C₄H₉; 5-decyn-4-one of formulaC₄H₉—C≡C—CO—C₃H₇; 2-decen-5-yn-4-one of formula C₄H₉—C≡C—CO—CH═CH—CH₃;1-(p-methoxyphenyl)-2-propyn-1-one of formula H₃C—O—C₆H₄—CO—C≡CH;1-cyclopropyl-2-heptyn-1-one of formula C₄H₉—C≡C—CO—C₃H₅ cyclopropyl);2-methyl-5-decyn-4-one of formula C₄H₉—C≡C—CO—CH₂—CH(CH₃)₂;9-methyl-5-decyn-4-one of formula C₃H₇—CO—C♭C—CH₂—CH₂—CH(CH₃)₂;2-methyl-4-octyn-3-one of formula C₃H₇—C≡C—CO—CH(CH₃)₂;1-phenyl-2-propyn-1-one of formula C₆H₅—CO—C≡CH; 4-phenyl-3-butyn-2-oneof formula C₆H₅—C≡C—CO—CH_(3;) 5-phenyl-4-pentyn-3-one of formulaC₆H₅—C≡C—CO—C₂H₅; 6-phenyl-5-hexyn-2,4-dione of formulaC₆H₅—C≡C—CO—CH₂—CO—CH₃; 1-phenyl-1-heptyn-3-one of formulaC₆H₅—C≡C—CO—C₄H_(9;) 1-(2-furyl)-3-phenyl-2-propyn-1-one of formulaC₆H₅—C≡C—CO—C₄H₃O furyl); 1-(2-furyl)-2-octyn-1-one of formulaC₅H₁₁—C≡C—CO—C₄H₃O (furyl); C₆H₅—C≡C—CO—C₄H₃O (furyl);3-cyclopropyl-1-(p-tolyl)-2-propyn-1-one of formulaC₃H₂—C≡C—CO—C₆H₄—CH₃; 1-cyclopropyl-4-methyl-1-hexyn-3 -one of formulaC₃H₅—C≡C—CO—CH(C₂H₅)—CH₃(cyclopropyl); 9-hexadecyn-8-one of formulaC₆H₁₃—C≡C—CO—C₇H₁₅; 5-ethyl-11-methyl-7-dodecyn-6-one of formula(CH₃)₂CH—C₂H₄—C≡C—CO—CH(C₂H₅)—C₄H₉; 7-tetradecyn-6-one of formulaC₆H₁₃—C≡C—CO—C₅H_(11;) 1-cyclohexyl-4-ethyl-1-hexyn-3-one of formulaC₆H₁₁—C≡C—CO—CH(C₂H₅)₂(cyclohexyl); 1-cyclopentyl-4-nonyn-3-one offormula C₄H₉—C≡C—CO—C₂H₄—C₅H₉(cyclopentyl); 1-cyclohexyl-2-heptyn-1-oneof formula C₄H₉—C≡C—CO—C₆H₁₁(cyclohexyl); 1-(p-tolyl)-2-butyn-1-one offormula CH₃—C≡C—CO—C₆H₄-(p-CH₃)_(;) 2,2,8-trimethyl-4-nonyn-3-one offormula (CH₃)₂CH—C₂H₄—C≡C—CO—C(CH₃)₃; 2,2-dimethyl-4-hexyn-3-one offormula CH₃—C≡C—CO—C(CH₃)_(3;) 1,4-diphenyl-2-butyn-1,4-dione of formulaC₆H₅—CO—C≡C—CO—C₆H₅; 5-decyn-2,4-dione of formulaC₄H₉—C≡C—CO—CH₂—CO—CH₃; 1-(3,4-dimethoxyphenyl)-2-butyn-1-one of formulaCH₃—C≡C—CO—C₆H₃—(OCH₃)₂; 2,5-heptadiyn-4-one of formulaH₃C—C≡C—CO—C≡C—CH_(3;) 3-hexyn-2,5-dione of formula CH₃—CO—C≡C—CO—CH₃;4-octyn-3,6-dione of formula C₂H₅—CO—C≡C—CO—C₂H₅;2,7-dimethyl-4-octyn-3,6-dione of formula (CH₃)₂CH—CO—C≡C—CO—CH(CH₃)₂;2,7-dimethyl-4-octyn-3-one of formula (CH₃)₂CH—CH₂—C≡C—CO—CH(CH₃)₂;4,7-undecadiyn-6-one of formula C₃H₇—C≡C—CO—C≡C—C₃H₇; 5-decyn-4,7-dioneof formula C₃H₇—CO—C≡C—CO—C₃H₇; 2,9-dimethyl-5-decyn-4,7-dione offormula (CH3)₂CH—CH₂—CO—C≡C—CO—CH₂—CH(CH₃)₂; 6-dodecyn-5,8-dione offormula C₄H₉—CO—C≡C—CO—C₄H_(9;) 2,11-dimethyl-6-dodecyn-5,8-dione offormula (CH₃)₂CH—C₂H₄—CO—C≡C—CO—(CH₂)₂—CH(CH₃);2,9-dimethyl-5-decyn-4-one of formula (CH₃)₂CH—C₂H₄—C≡C—CO—CH₂—CH(CH₃)₂;7-tetradecyn-6,9-dione of formula C₅H₁₁—CO—C≡C—CO—C₅H_(11;)4,10-undecadiyn-3-one of formula HC≡C—C₄H₈—C≡C—CO—C₂H₅;2,12-dimethyl-7-oxa-4,9-tridecadiyn-3,11-dione of formula(CH₃)₂—CO—C≡C—CH₂—O—CH₂—C≡C—CO—CH(CH₃)₂; and4,10-tetradecadiyn-3,12-dione of formula C₂H₅—CO—C≡C—C₄H₈—C≡C—CO—C₂H₅.29. The method of claim 27, wherein the compound of formula 1 is a pairof compounds of formula 1 selected from the group consisting of thepairs 1-phenyl-2-propyn-1-one/1-decyn-3-one;1-(2-furyl)-2-octyn-1-one/1-decyn-3-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-decyn-3-one;1-octyn-3-one/1-decyn-3-one; 1-(p-tolyl)-2-butyn-1-one/1-decyn-3-one;2,5-heptadiyn-4-one/1-decyn-3-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-decyn-3-one;1,4-diphenyl-2-butyn-1,4-dione/1-decyn-3-one;4,7-undecadiyn-6-one/1-decyn-3-one;1-(2-furyl)-2-octyn-1-one/1-phenyl-2-propyn-1-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-phenyl-2-propyn-1-one;1-octyn-3-one/1-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-phenyl-2-propyn-1-one;2,5-heptadiyn-4-one/1-phenyl-2-propyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-phenyl-2-propyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-phenyl-2-propyn-1-one;4,7-undecadiyn-6-one/1-phenyl-2-propyn-1-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-(2-furyl)-2-octyn-1-one;1-octyn-3-one/1-(2-furyl)-2-octyn-1-one 1-(p-tolyl)-2-butyn-1-one;2,5-heptadiyn-4-one/1-(2-furyl)-2-octyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(2-furyl)-2-octyn-1-one1,4-diphenyl-2-butyn-1,4-dione/1-(2-furyl)-2-octyn-1-one;4,7-undecadiyn-6-one/1-(2-furyl)-2-octyn-1-one;1-octyn-3-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;2,5-heptadiyn-4-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-(2-furyl)-3-phenyl-2-propyn-1-one;4,7-undecadiyn-6-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-octyn-3-one;2,5-heptadiyn-4-one/1-octyn-3-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-octyn-3-one;1,4-diphenyl-2-butyn-1,4-dione/1-octyn-3-one;4,7-undecadiyn-6-one/1-octyn-3-one;2,5-heptadiyn-4-one/1-(p-tolyl)-2-butyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(p-tolyl)-2-butyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-(p-tolyl)-2-butyn-1-one;4,7-undecadiyn-6-one/1-(p-tolyl)-2-butyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/2,5-heptadiyn-4-one;1,4-diphenyl-2-butyn-1,4-dione/2,5-heptadiyn-4-one;4,7-undecadiyn-6-one/2,5-heptadiyn-4-one;1,4-diphenyl-2-butyn-1,4-dione/1-(p-methoxyphenyl)-2-propyn-1-one;4,7-undecadiyn-6-one/1-(p-methoxyphenyl)-2-propyn-1-one; and4,7-undecadiyn-6-one/1,4-diphenyl-2-butyn-1,4-dione.
 30. The method ofclaim 27, wherein the compound of formula 1 is in the composition in aquantity comprised between 0.1% and 40%, preferentially between 0.1% and10%, of the total weight of the composition.
 31. The method of claim 27,wherein said composition further comprises at least one aldehydeselected from the group consisting of the acyclic and non-terpenicaliphatic aldehydes, the non-terpenic alicyclic aldehydes, the terpenicaldehydes, the aliphatic aldehydes substituted by an aromatic group, thebifunctional aldehydes, the aldehydes possessing a non-aromaticunsaturation borne by the carbon in the alpha position of the aldehydefunction, the aldehydes possessing an unsaturation in the alpha positionof the aldehyde function conjugated with an aromatic ring and thealdehydes the function of which is borne by an aromatic ring, and evenmore preferentially in a deodorant composition comprising a mixture ofat least one first aldehyde (aldehyde of class A) selected from thegroup consisting of the acyclic and non-terpenic aliphatic aldehydes,the non-terpenic alicyclic aldehydes, the terpenic aldehydes, thealiphatic aldehydes substituted by an aromatic group and thebifunctional aldehydes and at least one second aldehyde (aldehyde ofclass B) selected from the group consisting of the aldehydes possessinga non-aromatic unsaturation borne by the carbon in the alpha position ofthe aldehyde function, the aldehydes possessing an unsaturation in thealpha position of the aldehyde function conjugated with an aromatic ringand the aldehydes the function of which is borne by an aromatic ring.32. The method of claim 31, wherein said composition comprises aquantity of the aldehyde comprised between 0.5% and 50% of thecomposition, preferentially in a quantity comprised between 1% and 20%of the composition.
 33. The method of claim 31, wherein the aldehydes ofclasses A and B are in proportions relative to each other in proportionsfrom 80/20 to 20/80 in particular in proportions of 50/50 and in a totalquantity of aldehydes comprised between 1% and 90% of the composition,preferentially in a quantity comprised between 10% and 30% of thecomposition.
 34. Deodorant composition comprising at least one compoundof the family of the α-acetylenic ketones corresponding to generalformula 1R—(CO)_(k)—C≡C-(A)-(C≡C)_(m)—(CO)_(n)—R₁   (1) selected from the groupconsisting of 1-octyn-3-one of formula C₅H₁₁—CO—C≡CH; 3-octyn-2-one offormula C₄H₉—C≡C—CO—CH_(3;) 4-octyn 3-one of formula C₃H₇—C≡C—CO—C₂H₅;4-nonyn-3-one of formula C₃H₇—CH₂—C≡C—CO—C₂H₅; 2-nonyn-4-one of formulaCH₃—C≡C—CO—O₅H₁₁; 5-nonyn-4-one of formula C₃H₇—CO—C≡C—CH₂—C₂H₅;1-decyn-3-one of formula C₇H₁₅—CO—C≡CH; 4-decyn-3-one of formulaC₅H₁₁—C≡C—CO—C₂H_(5;) 6-decyn-5-one of formula C₃H₇—C≡C—CO—C₄H₉;5-decyn-4-one of formula C₄H₉—C≡C—CO—C₃H₇; 1-cyclopropyl-2-heptyn-1-oneof formula C₄H₉—C≡C—CO—C₃H₅ cyclopropyl); 2-methyl-5-decyn-4-one offormula C₄H₉—C≡C—CO—CH₂—CH(CH₃)₂; 9-methyl-5-decyn-4-one of formulaC₃H₇—CO—C≡C—CH₂—CH₂—CH(CH₃)_(2;) 2-methyl-4-octyn-3-one of formulaC₃H₇—C≡C—CO—CH(CH₃)₂; 4-phenyl-3-butyn-2-one of formulaC₆H₅—C≡C—CO—CH_(3;) 5-phenyl-4-pentyn-3-one of formula C₆H₅—C≡C—CO—C₂H₅;1-phenyl-1-heptyn-3-one of formula C₆H₅—C≡C—CO—C₄H_(9;)1-cyclopropyl-4-methyl-1-hexyn-3-one of formulaC₃H₅—C≡C—CO—CH(C₂H₅)—CH₃(cyclopropyl); 9-hexadecyn-8-one of formulaC₆H₁₃—C≡C—CO—C₇H₁₅; 5-ethyl-11-methyl-7-dodecyn-6-one of formula(CH₃)₂CH—C₂H₄—C≡C—CO—CH(C₂H₅)—C₄H_(9;) 7-tetradecyn-6-one of formulaC₆H₁₃—C≡C—CO—C₅H_(11;) 1-cyclohexyl-4-ethyl-1-hexyn-3-one of formulaC₆H₁₁—C≡C—CO—CH(C₂H₅)₂(cyclohexyl); 1-cyclopentyl-4-nonyn-3-one offormula C₄H₉—C≡C—CO—C₂H₄—C₅H₉(cyclopentyl); 1-cyclohexyl-2-heptyn-1-oneof formula C₄H₉—C≡C—CO—C₆H₁₁(cyclohexyl); 2,2,8-trimethyl-4-nonyn-3-oneof formula (CH₃)₂CH—C₂H₄—C≡C—CO—C(CH₃)₃; 2,2-dimethyl-4-hexyn-3-one offormula CH₃—C≡C—CO—C(CH₃)_(3;) 3-hexyn-2,5-dione of formulaCH₃—CO—C≡C—CO—CH₃; 4-octyn-3,6-dione of formula C₂H₅—CO—C≡C—CO—C₂H₅;2,7-dimethyl-4-octyn-3,6-dione of formula (CH₃)₂CH—CO—C≡C—CO—CH(CH₃)₂;2,7-dimethyl-4-octyn-3-one of formula (CH₃)₂CH—CH₂—C≡C—CO—CH(CH₃)₂;4,7-undecadiyn-6-one of formula C₃H₇—C≡C—CO—C≡C—C₃H₇; 5-decyn-4,7-dioneof formula C₃H₇—CO—C≡C—CO—C₃H₇; 2,9-dimethyl-5-decyn-4,7-dione offormula (CH₃)₂CH—CH₂—CO—C≡C—CO—CH₂—CH(CH₃)₂;2,11-dimethyl-6-dodecyn-5,8-dione of formula(CH₃)₂CH—C₂H₄—CO—C≡C—CO—(CH₂)₂—CH(CH₃); 2,9-dimethyl-5-decyn-4-one offormula (CH₃)₂CH—C₂H₄—C≡C—CO—CH₂—CH(CH₃)₂; 7-tetradecyn-6,9-dione offormula C₅H₁₁—CO—C≡C—CO—C₅H_(11;) 4,10-undecadiyn-3-one of formulaHC≡C—C₄H₈—C≡C—CO—C₂H₅; 2,12-dimethyl-7-oxa-4,9-tridecadiyn-3,11-dione offormula (CH₃)₂—CO—C≡C—CH₂—O—CH₂—C≡C—CO—CH(CH₃)₂; and4,10-tetradecadiyn-3,12-dione of formula C₂H₅—CO—C≡C—C₄H₈—C≡C—CO—C₂H₅.35. Deodorant composition comprising at least one compound of formula 1R—(CO)_(k)—C≡C-(A)-(C≡C)_(m)—(CO)_(n)—R₁   (1) selected from the groupconsisting of the pairs 1-phenyl-2-propyn-1-one/1-decyn-3-one;1-(2-furyl)-2-octyn-1-one/1-decyn-3-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-decyn-3-one;1-octyn-3-one/1-decyn-3-one; 1-(p-tolyl)-2-butyn-1-one/1-decyn-3-one;2,5-heptadiyn-4-one/1-decyn-3-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-decyn-3-one;1,4-diphenyl-2-butyn-1,4-dione/1-decyn-3-one;4,7-undecadiyn-6-one/1-decyn-3-one;1-(2-furyl)-2-octyn-1-one/1-phenyl-2-propyn-1-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-phenyl-2-propyn-1-one;1-octyn-3-one/1-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-phenyl-2-propyn-1-one;2,5-heptadiyn-4-one/1-phenyl-2-propyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-phenyl-2-propyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-phenyl-2-propyn-1-one;4,7-undecadiyn-6-one/1-phenyl-2-propyn-1-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-(2-furyl)-2-octyn-1-one;1-octyn-3-one/1-(2-furyl)-2-octyn-1-one 1-(p-tolyl)-2-butyn-1-one;2,5-heptadiyn-4-one/1-(2-furyl)-2-octyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(2-furyl)-2-octyn-1-one1,4-diphenyl-2-butyn-1,4-dione/1-(2-furyl)-2-octyn-1-one;4,7-undecadiyn-6-one/1-(2-furyl)-2-octyn-1-one;1-octyn-3-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;2,5-heptadiyn-4-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-(2-furyl)-3-phenyl-2-propyn-1-one;4,7-undecadiyn-6-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-octyn-3-one;2,5-heptadiyn-4-one/1-octyn-3-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-octyn-3-one;1,4-diphenyl-2-butyn-1,4-dione/1-octyn-3-one;4,7-undecadiyn-6-one/1-octyn-3-one;2,5-heptadiyn-4-one/1-(p-tolyl)-2-butyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(p-tolyl)-2-butyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-(p-tolyl)-2-butyn-1-one;4,7-undecadiyn-6-one/1-(p-tolyl)-2-butyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/2,5-heptadiyn-4-one;1,4-diphenyl-2-butyn-1,4-dione/2,5-heptadiyn-4-one;4,7-undecadiyn-6-one/2,5-heptadiyn-4-one;1,4-diphenyl-2-butyn-1,4-dione/1-(p-methoxyphenyl)-2-propyn-1-one;4,7-undecadiyn-6-one/1-(p-methoxyphenyl)-2-propyn-1-one; and4,7-undecadiyn-6-one/1,4-diphenyl-2-butyn-1,4-dione.
 36. Deodorantcomposition comprising at least one compound of formula 1R—(CO)_(k)—C≡C-(A)-(C≡C)_(m)—(CO)_(n)—R₁   (1) in which R and R₁ canrepresent, independently or simultaneously, a radical selected from thegroup consisting of an alkyl chain comprising from 1 to 9,preferentially from 3 to 7 carbon atoms, linear or branched, substitutedor unsubstituted, or a cycloalkane comprising from 3 to 8,preferentially from 5 or 6 carbon atoms, substituted or unsubstituted;or a furan ring, saturated or unsaturated, substituted or unsubstituted;or a pyran ring, saturated or unsaturated, substituted or unsubstituted;or an aromatic ring comprising from 6 to 8 carbon atoms, substituted orunsubstituted; and a hydrogen atom, A represents a group selected fromthe group consisting of —(CH₂)_(x) with x representing an integer with avalue from 0 to 6, preferentially from 0 to 4, (—CO)₁ with 1representing an integer with a value of 0 or 1, and a—(CH₂)_(y)—O—(CH₂)_(z)— chain formation with y and z representing,simultaneously or independently, an integer with a value from 0 to 6,preferentially from 0 to 4, wherein x+y does not exceed the value of 6;k, m and n are, simultaneously or independently, an integer with a valueof 0 or 1, wherein k and n do not simultaneously have a value of 0 if 1is equal to 0; with the exception of 2-methyl-4-nonyn-3-one of formulaC₄H₉—C≡C—CO—CH(CH₃)₂ and at least one aldehyde selected from the groupconsisting of acyclic and non-terpenic aliphatic aldehydes, thenon-terpenic alicyclic aldehydes, the terpenic aldehydes, the aliphaticaldehydes substituted by an aromatic group, the bifunctional aldehydes,the aldehydes possessing a non-aromatic unsaturation borne by the carbonin the alpha position of the aldehyde function, the aldehydes possessingan unsaturation in the alpha position of the aldehyde functionconjugated with an aromatic ring and the aldehydes the function of whichis borne by an aromatic ring, and even more preferentially in adeodorant composition comprising a mixture of at least one firstaldehyde (aldehyde of class A) selected from the group consisting of theacyclic and non-terpenic aliphatic aldehydes, the non-terpenic alicyclicaldehydes, the terpenic aldehydes, the aliphatic aldehydes substitutedby an aromatic group and the bifunctional aldehydes and at least onesecond aldehyde (aldehyde of class B) selected from the group consistingof aldehydes possessing a non-aromatic unsaturation borne by the carbonin the alpha position of the aldehyde function, the aldehydes possessingan unsaturation in the alpha position of the aldehyde functionconjugated with an aromatic ring and the aldehydes the function of whichis borne by an aromatic ring.
 37. The method of claim 28, wherein thecompound of formula 1 is a pair of compounds of formula 1 selected fromthe group consisting of the pairs 1-phenyl-2-propyn-1-one/1-decyn-3-one;1-(2-furyl)-2-octyn-1-one/1-decyn-3-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-decyn-3-one;1-octyn-3-one/1-decyn-3-one; 1-(p-tolyl)-2-butyn-1-one/1-decyn-3-one;2,5-heptadiyn-4-one/1-decyn-3-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-decyn-3-one;1,4-diphenyl-2-butyn-1,4-dione/1-decyn-3-one;4,7-undecadiyn-6-one/1-decyn-3-one;1-(2-furyl)-2-octyn-1-one/1-phenyl-2-propyn-1-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-phenyl-2-propyn-1-one;1-octyn-3-one/1-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-phenyl-2-propyn-1-one;2,5-heptadiyn-4-one/1-phenyl-2-propyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-phenyl-2-propyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-phenyl-2-propyn-1-one;4,7-undecadiyn-6-one/1-phenyl-2-propyn-1-one;1-(2-furyl)-3-phenyl-2-propyn-1-one/1-(2-furyl)-2-octyn-1-one;1-octyn-3-one/1-(2-furyl)-2-octyn-1-one 1-(p-tolyl)-2-butyn-1-one;2,5-heptadiyn-4-one/1-(2-furyl)-2-octyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(2-furyl)-2-octyn-1-one1,4-diphenyl-2-butyn-1,4-dione/1-(2-furyl)-2-octyn-1-one;4,7-undecadiyn-6-one/1-(2-furyl)-2-octyn-1-one;1-octyn-3-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;2,5-heptadiyn-4-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-(2-furyl)-3-phenyl-2-propyn-1-one;4,7-undecadiyn-6-one/1-(2-furyl)-3-phenyl-2-propyn-1-one;1-(p-tolyl)-2-butyn-1-one/1-octyn-3-one;2,5-heptadiyn-4-one/1-octyn-3-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-octyn-3-one;1,4-diphenyl-2-butyn-1,4-dione/1-octyn-3-one;4,7-undecadiyn-6-one/1-octyn-3-one;2,5-heptadiyn-4-one/1-(p-tolyl)-2-butyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/1-(p-tolyl)-2-butyn-1-one;1,4-diphenyl-2-butyn-1,4-dione/1-(p-tolyl)-2-butyn-1-one;4,7-undecadiyn-6-one/1-(p-tolyl)-2-butyn-1-one;1-(p-methoxyphenyl)-2-propyn-1-one/2,5-heptadiyn-4-one;1,4-diphenyl-2-butyn-1,4-dione/2,5-heptadiyn-4-one;4,7-undecadiyn-6-one/2,5-heptadiyn-4-one;1,4-diphenyl-2-butyn-1,4-dione/1-(p-methoxyphenyl)-2-propyn-1-one;4,7-undecadiyn-6-one/1-(p-methoxyphenyl)-2-propyn-1-one; and4,7-undecadiyn-6-one/1,4-diphenyl-2-butyn-1,4-dione.
 38. The method ofclaim 32, wherein the aldehydes of classes A and B are in proportionsrelative to each other in proportions from 80/20 to 20/80 in particularin proportions of 50/50 and in a total quantity of aldehydes comprisedbetween 1% and 90% of the composition, preferentially in a quantitycomprised between 10% and 30% of the composition.